


The Punishment

by BottomDean67



Category: Supernatural
Genre: Addiction, Anal Fingering, Anal Sex, Bestiality, Bottom Dean Winchester, Bottom Dean Winchester/Top Sam Winchester, Boy King of Hell Sam Winchester, Cock Cages, Cock Slut Dean Winchester, Collars, Consensual Non-Consent, Demon Dean Winchester, Dildos, Dirty Talk, Dom/sub, Drug Use, Face-Fucking, Fucking Machines, Gags, Knotting Dildos, M/M, Oral Sex, Orgasm Denial, Painplay, Restraints, Roleplay, Smut, Top Sam Winchester, hole spanking
Language: English
Status: Completed
Published: 2019-12-08
Updated: 2019-12-08
Packaged: 2021-02-25 22:01:02
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,844
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21722644
Author URL: https://archiveofourown.org/users/BottomDean67/pseuds/BottomDean67
Summary: Demon!Dean made a mistake when he got his brother addicted to demon blood again. Now Sam is the all powerful boyking of Hell and he wants Dean good and trained for being the best cockslut there ever was.
Relationships: Dean Winchester/Sam Winchester
Comments: 7
Kudos: 332





	The Punishment

To say Dean’s plan had not gone well would have been an understatement. Demon cuffs restained his hands behind his back and kept him powerless and weak. They had not once come off since they’d gone on and Dean had a feeling they never would.

He sighed when the door to the dungeon opened and Sam came in, a smirk on his face.

“Hello, big brother,” said Sam, quickly walking inside and over to Dean. He grabbed Dean’s short strands and tilted his head to the side. He bit into the tender flesh of Dean’s neck, breaking skin and feasting on Dean’s blood until he got light headed. 

Dean dropped his head and shut his eyes, Sam petting his hair gently.

“Good, Dean. I know you’re still getting used to the way things are, the way your little plan to control me didn’t work out. I’m guessing you didn’t realize that once you got me addicted to demon blood again, I’d end up stronger than you, huh,” said Sam. 

Dean was silent. Silence normally worked out better for him.

“My demons need a way to work out their aggression and you need to learn your place,” said Sam. Dean whipped his head up and Sam snapped his fingers.

Suddenly he was very aware of the fact he was naked and very aware of the fact he was secured to some kind of bench. His legs were spread and head tilted up. Some kind of gag was in his mouth forcing his jaw open and his cock hurt fiercely.

“There are far easier ways to do this but I prefer to...train the response out of you,” said Sam as he walked in front of him. Dean narrowed his eyes as he felt his cock start to burn. “You’re in Hell. I know you recognize it. This will take as long as it takes.”

Dean did his best to swallow but felt some drool drip down his chin.

“I would do your best to not become aroused. It’ll be most unpleasant. I’ll return when you’re trained,” he said. Dean watched Sam disappear in front of him and frowned, or at least tried to. 

“Looks like the new boss left us a present,” said a demon behind him. Dean would have made a snarky comment back but something wet pushed at his hole and Dean grunted, pain flaring up inside him as something was forced in deep. 

He screamed into his gag when it doubled in size all of a sudden.

“Oh, don’t be such a baby,” said the demon. The object seemed to rotate around and squirted something something inside of him. Dean had a feeling it wasn’t lube. Demons would never be that kind. 

It grew quiet and Dean figured the demon had left him alone for some strange reason. Whatever was going on, it wasn’t like the first time he’d been in Hell. He’d already been fucked senseless that time. Another squirt of cool liquid in him made him shudder.

At least he wasn’t getting nailed in the ass. Yet.  
  


“I think that about does it,” said a demon all of a sudden. Dean opened his eyes slowly, the device shrinking back down and being removed from his hole. To his surprise, it tightened back up immediately. “I know you’re confused but boss for some reason wanted you trained all nice and shit. Personally, I don’t agree but he makes the rules.”

Dean rolled his eyes, feeling a slow pressure build at his asshole, a large dildo slipping inside. It pressed right up against his prostate and Dean groaned.

“Don’t even start,” he said. He moved around and placed a cock cage around Dean’s cock and balls, locking it tight. Dean took a deep breath, feeling the sharp prick of spikes on the inside of the metal. The second his cock even thought about getting hard, it’d dig into his flesh.

The demon positioned a fake cock at Dean’s lips and slipped the head inside his mouth, lips stretched out perfectly.

“You’re gonna be such a good cock sucker by the time you’re done with training,” he said. He flipped a switch and the dildo in his mouth started thrusting inside slowly. 

The one in his ass was pounding harder though and Dean winched when his poor abused prostate was hit. His cock tried to get hard but the sharp pricks along the cage bit into his dick and made him howl around the dildo in his mouth.

“Here’s the thing, Dean. Sam likes you the way you are. He don’t want you changed a bit. He wants you to be his bitch though and the thing is, bitches don’t come. Removal is far easier but he wants the response  _ trained _ out so that’s what we’ll do. That funny thing from before? One teensey little jump start. Think of it as medicine. Your body will have an...allergic reaction to coming. It’s going to want to come. In fact it will, every fifteen or so minutes for...quite a long time, even with that pretty little locked up dick of yours. But that cock cage is going to hurt. You’re going to get hard and it’ll hurt and hurt and you’ll keep coming. See, your body will learn that coming and an orgasm means extreme pain. When training is through, your cock won’t even be  _ able _ to get hard. You could have the best blow job in the world and it’ll stay nice and soft. Enjoy the medicine while it lasts Dean. Your training will be the last time you orgasm again.”

  
  


After a few hours, Dean didn’t bother to keep his eyes open. His cock was numb from pain, the dildo in his ass still fucking into him without pause, the dildo in his mouth occassionally spewing out real cum. Dean suckled it down. There was nothing else to do.

There was no escape, even as a demon. He tried to will himself to sleep through it all.  
  


**One Month Later**

“Good boy,” said the demon that’d been training Dean. Dean greedily sucked at his cock while riding the dildo in his ass. His hands were secured behind his back in thick leather cuffs, ingraved with enough sigils to keep Dean completely powerless. “Sit.”

Dean sat back on the dildo, staring up as the demon came over Dean’s face. Dean felt it drip down to his chest but he didn’t mind. He was used to it.

“Clean,” he said. Dean leaned forward and licked the cum off of the demon’s cock, keeping the cock in his mouth and nursing it while the demon ran a hand over his head. “I know you are a cum hungry cock slut but I want you to stop.”

Dean moved his mouth away, staring up through his eyelashes. The demon moved behind Dean and pushed him forward so he was presenting his ass, the tip of the dildo still buried inside his hole. Dean shuddered when a finger traced his permanently red and puffy rim.

“Off,” he said. Dean shifted forward and the dildo slipped free. The demon moved Dean to the center of the room and clipped his collar to a bolt in the floor, a spreader bar keeping Dean’s legs wide open. Another dildo was presented at Dean’s ass. He whimpered as the soda can sized dildo was forced inside roughly, stopping when Dean felt the bulge part way down.

Knot fucking. The one thing he hadn’t yet learned to fake.

“I know you aren’t broken, Dean,” he said, storking Dean’s cock through the bars of the cage. The cock ring had rendered has balls useless at this point. Dean didn’t feel anything from them anymore. But his cock wasn’t willing to give up yet.

Dean was still torn on that.

“Oh, I know you think something is going to happen. I bet you think you know exactly what’s going to happen. You couldn’t be more wrong,” said the demon. A cold and smelly substance filled his ass, quickly absorbed and the dildo removed. “The hellhounds need a new bitch and lucky for them, you smell like you’re in heat.”

Dean’s eyes flew open and he shook his head. The demon only smiled as he removed the lubricating dildo and went to the door.

“There are plenty of hounds to keep you occupied. Don’t worry. We wouldn’t want yout little asshole to get a break from being fucked, would we?”  
  


“How many has he taken?” asked a demon that ran the kennel, poking his head into Dean’s training room.

“Lost count. Over a hundred. He is swollen with doggie cum,” smirked the demon, watching Dean sniffle as his ass was wrecked again. “I want every stud to have a go at him, no breakage.”

“You realize that’s gonna take awhile,” he said.

“I want Dean Winchester fucked so hard his cock will never think about getting hard again.”  
  


Dean had taken every last hellhound in hell. He had spent countless days with fucking machines and getting railed by demon after demon. His cock would not for the life of him stop trying to get hard though.

“Sammy,” Dean whispered one night, eyes screwed shut as a vibrating dildo buzzed against his prostate. “Please Sammy. I need you.”

“Yes, Dean?”

Dean flew open his eyes, blinking a few times before he saw Sam kneeling down in his cell.

“I miss you.”

Sam smiled and ran a hand over Dean’s head.

“I miss you as well. Are you finished with your training?”

“No. They’ll never finish with it,” Dean mumbled. 

“They will finish when you are done being trained. So, are you done being trained, Dean?” asked Sam. Dean swallowed and stared up at him.

“My cock keeps getting hard,” said Dean.

“You cock belongs to me Dean. I like that it gets hard. I like that you do not come. I am very satisfied with these things,” said Sam. “Do you honestly think that you are not exactly what I want?”

“I wanted to kill you,” said Dean.

“You didn’t want to worry about me anymore but here’s the thing. I’m stronger than you, I’m more powerful than you. You don’t have to worry ever again. I will take care of you. I will run Hell with you by my side. Your blood will give me power and you will be owned the way you so desperately need to be. So I’ll ask again, are you done with training?”

Dean nodded and Sam smiled. Instantly Dean found himself in a warm room, on a soft bed, everything gone. His body didn’t hurt for the first time in who knew how long.

“Dean,” said Sam. Dean immediately sat up in bed and spotted Sam standing nearby. “Suck me.”

Dean shifted off the bed and down to his knees, crawling over to Sam. Carefully he slid his hands up the pair of long legs, expertly undoing the belt and zipper. Dean leaned in as he pulled down Sam’s jeans and underwear, lips wrapping gently around the tip of his cock.

“I know you’ve wanted this for a very long time, Dean. Us. Together. It may not be what you envisioned but this can be even better. I’d prefer a willing partner.”

Dean sat back on his heels, looking up at Sam, letting the half-hard cock fall from his lips. Dean grabbed Sam’s hips and pushed him back towards the bed, Sam allowing it as Dean seemed to settle back in between his legs. Dean licked a line up Sam’s cock and suckled on the tip, lapping up the precome. He looked up to Sam, mouth stuffed full of dick and offered his arm. Sam took it and brought it to his lips, Dean giving a nod. Sam bit into the flesh, warm blood filling his mouth just as Dean started to deep throat him.

He came far too quickly, the high of his orgasm and the blood making him nearly pass out. Sam fluttered his eyes and pulled Dean up onto the bed, drinking more blood before he pushed the arm away and used his powers to heal it.

“You could have just asked next time,” said Sam, smirking as he rolled over and pinned Dean playfully beneath him. 

“Where’s the fun in that?” teased Dean. Sam gave him a hungry kiss that Dean returned, licking his lips when Sam broke it off. “I didn’t realize fucking you would get me my ass pounded by every hellhound to exist.”

“You loved it and you know it,” said Sam. “Also it was not every hellhound. Just thirty eight.”

“Oh, was that all?” laughed Dean, Sam giving his wrists a light squeeze. “How long was it?”

“About twelve hours. How long did the spell make you think?” he asked.

“Years.”

“You are a glutton for punishment,” said Sam, kissing Dean’s jaw. “Kinkiest fucker there ever was.”

“I’m the kinky one.  _ Right _ ,” laughed Dean.

“Said the bottomiest bitch to ever bottom,” said Sam. “Do you know _how_ _much_ research I had to do to make your head think half the shit you thought was happening was happening? Next time you need a punishment, I’m spanking your hole and calling it a night.”

“Is that a promise?” asked Dean. “I’ll fuck you in your sleep tonight if that’s the reward, should I say punishment, I’ll be receiving.”

“I say first off, fucking me in my sleep is okay if you ask beforehand and second, get on your stomach and spread your cheeks. I’m spanking your hole for good measure,” said Sam.

“Did I upset the boyking of Hell?” teased Dean.

“You  _ will _ regret that. Now I’m not telling you how many you’re getting,” said Sam. “Present.”

Dean grumbled but rolled onto his stomach when Sam stood up. He heard him remove his belt from the loops, likely folding it before Dean felt the cool leather rub over his hole.

“There’s no need to count for me. Lay there and take it,” said Sam.

Dean swallowed, his hands keeping his cheeks spread. The first crack came down hard, Dean biting the covers of the bedspread. Damn, Sam always knew how to make him come undone from this. 

The hits came in rapid succession, Dean’s jaw dropping open, tears welling in his eyes. Sam didn’t stop though and quickly Dean was crying quietly, the hits coming fast and hard until Dean whined and felt a felt a soft hand in his hair.

“Wow. Thirty on your hole. You’ve never done that many before,” said Sam, turning Dean over and kissing away his tears. “I’m so proud of you.”

“It hurts so much,” said Dean, burying his face in Sam’s neck.

“You can heal yourself if you’d like,” said Sam.

“...After you finger me?” asked Dean.

“Someone’s a painslut tonight,” said Sam. He shoved two dry fingers in Dean’s red and puffy hole, Dean shouting as Sam thrust roughly. “Aren’t you little _bitch_?”

“Yes,” breathed out Dean, crying again as Sam grabbed his cock. Sam started to stroke it with firm grips, going too hard but he didn’t seem to care. 

“I expect an answer.”

“I’m your little bitch,” said Dean, wincing as Sam shoved three fingers in him now, the tug on Dean’s cock becoming more prominent. “Sam!”

Dean nearly squirmed away when four of Sam’s massive fingers breached his hole, Sam’s hot breath fanning over Dean’s face.

“Come for me, bitch. _Now_.”

Dean moaned as he came all over Sam’s hand, temporarily forgetting about the pain as he got his orgasm. He was breathing hard when he felt Sam shift away, a hand on his forehead soon afterwards. The burning turned into a small ache in his ass, a reminder of where Sam had been. 

“Thanks, Sammy,” said Dean.

“Can I have a little more?” asked Sam.

“You never have to ask,” said Dean, laying his arm out over Sam’s chest. Sam bit into his arm once more, drinking slowly. 

“You are perfect,” said Sam when he finished, Dean a little high and floaty feeling himself.

“I know,” said Dean with a laugh. “Thanks for today, Sammy. I know roleplay ain’t your thing.”

“Anything for you, De,” said Sam. “Time for bed.”

Dean shifted back and slid Sam’s cock in his ass, Sam smiling as Dean pulled his arms up to his chest. Sam wrapped his arm around them, pining them in place as he lazily thrust into Dean. He toyed with Dean’s cock with his free hand but Sam wasn’t giving him another ograsm tonight.

Dean sank into it and sighed, his ass working Sam’s cock when Sam finally decided to come in Dean.

“Gonna keep my cum and cock warm all night like a good boy?” murmured Sam. He relaxed his hold on Dean so they could sleep. “Can’t sleep anymore unless you got a fresh load and cock filling you up, isn’t that right?”

“Mhm,” hummed Dean. Sam smirked and kissed Dean’s shoulder as he fell asleep.

He’d wake him up with a good hard fucking in the morning.


End file.
